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27468

Sigma-Aldrich

(−)-Citronellal

purum, ≥98.0% (sum of enantiomers, GC)

Synonym(s):

(S)-3,7-Dimethyl-6-octenal

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About This Item

Empirical Formula (Hill Notation):
C10H18O
CAS Number:
5949-05-3
Molecular Weight:
154.25
Beilstein/REAXYS Number:
1720790
EC Number:
227-707-9
MDL number:
MFCD00075588
UNSPSC Code:
12352114
PubChem Substance ID:
329752995

grade

purum

assay

≥98.0% (sum of enantiomers, GC)

optical activity

[α]20/D −16±1°, neat

refractive index

n20/D 1.447

density

0.851 g/mL at 20 °C (lit.)

SMILES string

C[C@@H](CC\C=C(\C)C)CC=O

InChI

1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3/t10-/m0/s1

InChI key

NEHNMFOYXAPHSD-JTQLQIEISA-N

replaced by

Product No.
Description
Pricing

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

167.0 °F - closed cup

flash_point_c

75 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Satish Chandra Philkhana et al.
Chemical communications (Cambridge, England), 49(32), 3342-3344 (2013-03-19)
Concise and protecting-group free synthesis of ent-palmyrolide A and (-)-cis-palmyrolide A were achieved starting from commercially available (S)-citronellal. The key fragment of palmyrolide A, "(5S,7S)-7-hydroxy-5,8,8-trimethylnonanamide", which makes up the most challenging part of the target molecule, was prepared in just
Gabriele Siedenburg et al.
Applied and environmental microbiology, 78(4), 1055-1062 (2011-12-14)
The biosynthesis of cyclic monoterpenes (C(10)) generally requires the cyclization of an activated linear precursor (geranyldiphosphate) by specific terpene cyclases. Cyclic triterpenes (C(30)), on the other hand, originate from the linear precursor squalene by the action of squalene-hopene cyclases (SHCs)
Kazumi Osada et al.
Chemical senses, 36(2), 137-147 (2010-10-20)
Body odors provide a rich source of sensory information for other animals. There is considerable evidence to suggest that short-term fluctuations in body odor can be caused by diet; however, few, if any, previous studies have demonstrated that specific compounds
Gabriele Siedenburg et al.
Applied microbiology and biotechnology, 97(4), 1571-1580 (2012-04-25)
Squalene-hopene cyclases (SHCs) are prokaryotic enzymes that catalyse the cyclisation of the linear precursor squalene to pentacyclic hopene. Recently, we discovered that a SHC cloned from Zymomonas mobilis (ZMO-1548 gene product) has the unique property to cyclise the monoterpenoid citronellal
Daniel P Iwaniuk et al.
Chemical communications (Cambridge, England), 48(91), 11226-11228 (2012-10-16)
A rationally designed stereodynamic ICD probe carrying two terminal amino functions for chemo- and enantioselective sensing of citronellal is introduced. The sensor shows strong Cotton effects upon diimine formation which can be used for accurate ee determination.
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